Sodium hydride → HCID 19919792, compound

HRID 1648525Notes

Reaction equation

HRID 1648525 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=2)[C:7](/[CH:10]=[C:11]2\[NH:12][C:13](=[O:17])[NH:14][C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[CH3:31][Si:32]([CH2:35][CH2:36][O:37][CH2:38]Cl)([CH3:34])[CH3:33]>CN(C=O)C>[CH2:1]([C:5]1[N:6]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=2)[C:7](/[CH:10]=[C:11]2\[NH:12][C:13](=[O:17])[N:14]([CH2:38][O:37][CH2:36][CH2:35][Si:32]([CH3:34])([CH3:33])[CH3:31])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 19086239HCID 19086239, compound

Product 1

HCID 19919792HCID 19919792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[(2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl]benzoate (0.200 g, 0.524 mmol) in DMF (2 mL) is added sodium hydride (80% in oil, 0.02 g, 0.67 mmol) and the mixture stirred for 5 minutes. (Trimethylsilyl)ethoxymethyl chloride SEM-C1 (0.100 mL, 0.536 mmol) is added and the mixture allowed to stir for 16 hours. The solvents are removed in vacuo and the residue dissolved in ethyl acetate and water. After drying the organic fraction over MgSO4, the required product is isolated by chromatography, eluting with 0.5% methanol in chloroform. Crystallized from ether.

Workup

  1. addition(0.100 mL, 0.536 mmol) is added
  2. stirringto stir for 16 hours
  3. customThe solvents are removed in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. dry with materialAfter drying the organic fraction over MgSO4

Sources & evidence

ORD record
ord-de845890a58c48fab02946360ff0c294
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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